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Volumn 30, Issue 5, 1997, Pages 219-225

The Claisen Rearrangement. Response to Solvents and Substituents: The Case for Both Hydrophobic and Hydrogen Bond Acceleration in Water and for a Variable Transition State

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EID: 0001423835     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar9600493     Document Type: Article
Times cited : (174)

References (75)
  • 1
    • 0000217402 scopus 로고
    • Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: New York
    • Wifp, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: New York, 1991; Vol. 5, pp 827. Ganem, B. Angew. Chem., Int. Ed. Engl. 1996, 35, 936.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 827
    • Wifp, P.1
  • 2
    • 0029789767 scopus 로고    scopus 로고
    • Wifp, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: New York, 1991; Vol. 5, pp 827. Ganem, B. Angew. Chem., Int. Ed. Engl. 1996, 35, 936.
    • (1996) Angew. Chem., Int. Ed. Engl. , vol.35 , pp. 936
    • Ganem, B.1
  • 4
    • 84982340618 scopus 로고
    • Vittorelli, P.; Winkler, T. Hansen H.-J.; Schmid, H. Helv. Chem. Acta 1968, 51, 1457. Hansen, H.-J.; Schmid, H. Tetrahedron 1974 30, 1959. Frater, G.; Habich, A.; Hansen, H.-J.; Schmid, H. Helv. Chim. Acta 1969, 52, 335, 1156. A helix arrangement of the heavy atoms can also rationalize the stereochemistry, but in the all-carbon variant of this reaction, this is a high-energy species presumably because of steric effects: Gajewski, J. J.; Benner, C. W.; Hawkins, C. M. J. Org. Chem. 1987, 52, 5198.
    • (1968) Helv. Chem. Acta , vol.51 , pp. 1457
    • Vittorelli, P.1    Winkler, T.2    Hansen, H.-J.3    Schmid, H.4
  • 5
    • 0001657403 scopus 로고
    • Vittorelli, P.; Winkler, T. Hansen H.-J.; Schmid, H. Helv. Chem. Acta 1968, 51, 1457. Hansen, H.-J.; Schmid, H. Tetrahedron 1974 30, 1959. Frater, G.; Habich, A.; Hansen, H.-J.; Schmid, H. Helv. Chim. Acta 1969, 52, 335, 1156. A helix arrangement of the heavy atoms can also rationalize the stereochemistry, but in the all-carbon variant of this reaction, this is a high-energy species presumably because of steric effects: Gajewski, J. J.; Benner, C. W.; Hawkins, C. M. J. Org. Chem. 1987, 52, 5198.
    • (1974) Tetrahedron , vol.30 , pp. 1959
    • Hansen, H.-J.1    Schmid, H.2
  • 6
    • 84980120337 scopus 로고
    • Vittorelli, P.; Winkler, T. Hansen H.-J.; Schmid, H. Helv. Chem. Acta 1968, 51, 1457. Hansen, H.-J.; Schmid, H. Tetrahedron 1974 30, 1959. Frater, G.; Habich, A.; Hansen, H.-J.; Schmid, H. Helv. Chim. Acta 1969, 52, 335, 1156. A helix arrangement of the heavy atoms can also rationalize the stereochemistry, but in the all-carbon variant of this reaction, this is a high-energy species presumably because of steric effects: Gajewski, J. J.; Benner, C. W.; Hawkins, C. M. J. Org. Chem. 1987, 52, 5198.
    • (1969) Helv. Chim. Acta , vol.52 , pp. 335
    • Frater, G.1    Habich, A.2    Hansen, H.-J.3    Schmid, H.4
  • 7
    • 0343747504 scopus 로고
    • Vittorelli, P.; Winkler, T. Hansen H.-J.; Schmid, H. Helv. Chem. Acta 1968, 51, 1457. Hansen, H.-J.; Schmid, H. Tetrahedron 1974 30, 1959. Frater, G.; Habich, A.; Hansen, H.-J.; Schmid, H. Helv. Chim. Acta 1969, 52, 335, 1156. A helix arrangement of the heavy atoms can also rationalize the stereochemistry, but in the all-carbon variant of this reaction, this is a high-energy species presumably because of steric effects: Gajewski, J. J.; Benner, C. W.; Hawkins, C. M. J. Org. Chem. 1987, 52, 5198.
    • (1987) J. Org. Chem. , vol.52 , pp. 5198
    • Gajewski, J.J.1    Benner, C.W.2    Hawkins, C.M.3
  • 12
    • 0012460869 scopus 로고
    • Gajewski, J. J.; Olson, L. P.; Tupper, K. J. J. Am. Chem. Soc. 1993, 115, 4548. Recent theoretical work on secondary isotope effects in the elimination reaction has generally confirmed the notion that transition state structure can be inferred reasonably at sites where bond breaking occurs between carbon and another heavy atom; however, when bond breaking occurs between carbon and hydrogen, the secondary effects at carbon do not correspond to the extent of bond breaking: Glad, S. S.; Jensen, F. J. Org. Chem. 1997, 62, 253. This is consistent with previous work on hydride additions from NADH to carbonyl groups where the secondary deuterium kinetic isotope effect is coupled with the hydride transfer motion so anomalogously high normal effects are observed: Huskey, W. P.; Schowen, R. L. J. Am. Chem. Soc. 1983, 105, 5704. Cha, Y.; Murray, C. J.; Klinman, J. P. Science 1989, 242, 1325.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 4548
    • Gajewski, J.J.1    Olson, L.P.2    Tupper, K.J.3
  • 13
    • 0002668332 scopus 로고    scopus 로고
    • Gajewski, J. J.; Olson, L. P.; Tupper, K. J. J. Am. Chem. Soc. 1993, 115, 4548. Recent theoretical work on secondary isotope effects in the elimination reaction has generally confirmed the notion that transition state structure can be inferred reasonably at sites where bond breaking occurs between carbon and another heavy atom; however, when bond breaking occurs between carbon and hydrogen, the secondary effects at carbon do not correspond to the extent of bond breaking: Glad, S. S.; Jensen, F. J. Org. Chem. 1997, 62, 253. This is consistent with previous work on hydride additions from NADH to carbonyl groups where the secondary deuterium kinetic isotope effect is coupled with the hydride transfer motion so anomalogously high normal effects are observed: Huskey, W. P.; Schowen, R. L. J. Am. Chem. Soc. 1983, 105, 5704. Cha, Y.; Murray, C. J.; Klinman, J. P. Science 1989, 242, 1325.
    • (1997) J. Org. Chem. , vol.62 , pp. 253
    • Glad, S.S.1    Jensen, F.2
  • 14
    • 0000809846 scopus 로고
    • Gajewski, J. J.; Olson, L. P.; Tupper, K. J. J. Am. Chem. Soc. 1993, 115, 4548. Recent theoretical work on secondary isotope effects in the elimination reaction has generally confirmed the notion that transition state structure can be inferred reasonably at sites where bond breaking occurs between carbon and another heavy atom; however, when bond breaking occurs between carbon and hydrogen, the secondary effects at carbon do not correspond to the extent of bond breaking: Glad, S. S.; Jensen, F. J. Org. Chem. 1997, 62, 253. This is consistent with previous work on hydride additions from NADH to carbonyl groups where the secondary deuterium kinetic isotope effect is coupled with the hydride transfer motion so anomalogously high normal effects are observed: Huskey, W. P.; Schowen, R. L. J. Am. Chem. Soc. 1983, 105, 5704. Cha, Y.; Murray, C. J.; Klinman, J. P. Science 1989, 242, 1325.
    • (1983) J. Am. Chem. Soc. , vol.105 , pp. 5704
    • Huskey, W.P.1    Schowen, R.L.2
  • 15
    • 0024573393 scopus 로고
    • Gajewski, J. J.; Olson, L. P.; Tupper, K. J. J. Am. Chem. Soc. 1993, 115, 4548. Recent theoretical work on secondary isotope effects in the elimination reaction has generally confirmed the notion that transition state structure can be inferred reasonably at sites where bond breaking occurs between carbon and another heavy atom; however, when bond breaking occurs between carbon and hydrogen, the secondary effects at carbon do not correspond to the extent of bond breaking: Glad, S. S.; Jensen, F. J. Org. Chem. 1997, 62, 253. This is consistent with previous work on hydride additions from NADH to carbonyl groups where the secondary deuterium kinetic isotope effect is coupled with the hydride transfer motion so anomalogously high normal effects are observed: Huskey, W. P.; Schowen, R. L. J. Am. Chem. Soc. 1983, 105, 5704. Cha, Y.; Murray, C. J.; Klinman, J. P. Science 1989, 242, 1325.
    • (1989) Science , vol.242 , pp. 1325
    • Cha, Y.1    Murray, C.J.2    Klinman, J.P.3
  • 16
    • 0040513008 scopus 로고
    • BEBOVIB: Sims, L. B.; Burton, G. W.; Lewis, D. E. QCPE No. 337, Department of Chemistry, Indiana University, Bloomington, IN 47405
    • Kupczyk-Subotkowska, L.; Saunders, W. H., Jr.; Shine, H. J.; Subotkowski, W. J. Am. Chem. Soc. 1993, 115, 5957. BEBOVIB: Sims, L. B.; Burton, G. W.; Lewis, D. E. QCPE No. 337, Department of Chemistry, Indiana University, Bloomington, IN 47405.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 5957
    • Kupczyk-Subotkowska, L.1    Saunders Jr., W.H.2    Shine, H.J.3    Subotkowski, W.4
  • 20
    • 0010421423 scopus 로고
    • Cramer, C. J., Truhlar, D. G., Eds.; ACS Symposium Series 568; American Chemical Society: Washington, DC
    • (b) Gajewski, J. J.; Brichford, N. L. In Structure and Reactivity in Aqueous Solution: Cramer, C. J., Truhlar, D. G., Eds.; ACS Symposium Series 568; American Chemical Society: Washington, DC, 1994; pp 229-242.
    • (1994) Structure and Reactivity in Aqueous Solution , pp. 229-242
    • Gajewski, J.J.1    Brichford, N.L.2
  • 21
    • 85033129016 scopus 로고
    • correction 1993, 26, 226
    • Dewar, M. J. S.; Jie, C. Acc. Chem. Res. 1992, 25, 5337; correction 1993, 26, 226. For efforts on the Claisen rearrangement see: Dewar, M. J. S.; Jie, C. J. Am. Chem. Soc. 1989, 111, 511.
    • (1992) Acc. Chem. Res. , vol.25 , pp. 5337
    • Dewar, M.J.S.1    Jie, C.2
  • 22
    • 0040513007 scopus 로고
    • Dewar, M. J. S.; Jie, C. Acc. Chem. Res. 1992, 25, 5337; correction 1993, 26, 226. For efforts on the Claisen rearrangement see: Dewar, M. J. S.; Jie, C. J. Am. Chem. Soc. 1989, 111, 511.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 511
    • Dewar, M.J.S.1    Jie, C.2
  • 24
    • 0001461906 scopus 로고
    • Wiest, O.; Black, K. A.; Houk, K. N. J. Am. Chem. Soc. 1994, 116, 10336. A reviewer has suggested that "the BeckeLYP functional has been unsuccessful for many transition state calculations".
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 10336
    • Wiest, O.1    Black, K.A.2    Houk, K.N.3
  • 29
    • 20644431615 scopus 로고
    • Kirkwood, J. G. J. Chem. Phys. 1934, 2, 351. Onsager, L. J. Am. Chem. Soc. 1936, 58, 1486.
    • (1934) J. Chem. Phys. , vol.2 , pp. 351
    • Kirkwood, J.G.1
  • 30
    • 0343791148 scopus 로고
    • Kirkwood, J. G. J. Chem. Phys. 1934, 2, 351. Onsager, L. J. Am. Chem. Soc. 1936, 58, 1486.
    • (1936) J. Am. Chem. Soc. , vol.58 , pp. 1486
    • Onsager, L.1
  • 32
    • 84948881009 scopus 로고
    • Cox, B. G.; Hedwig, G. R.; Parker, A. J.; Watts, D. W. Aust. J. Chem. 1974, 27, 477. Marcus, Y. Pure Appl. Chem. 1983, 55, 977.
    • (1983) Pure Appl. Chem. , vol.55 , pp. 977
    • Marcus, Y.1
  • 33
    • 0000593549 scopus 로고
    • Gajewski, J. J. J. Org. Chem. 1992, 57, 5500. For a more refined version of these parameters see ref 12b.
    • (1992) J. Org. Chem. , vol.57 , pp. 5500
    • Gajewski, J.J.1
  • 34
    • 0003436609 scopus 로고
    • Van Nostrand-Reinhold; Princeton
    • Hildebrand, J. H.; Prousnitz, J. M.; Scott, R. L. Regular and Related Solutions; Van Nostrand-Reinhold; Princeton, 1970. Hildebrand, J. H.; Scott, R. L. Regular Solutions; Prentice-Hall: Englewood Clifts, NJ., 1962. The solvent CED is the solvent heat of vaporization minus RT divided by the molar volume. For water the value in pressure units is 22,000 atm!
    • (1970) Regular and Related Solutions
    • Hildebrand, J.H.1    Prousnitz, J.M.2    Scott, R.L.3
  • 35
    • 0004110140 scopus 로고
    • Prentice-Hall: Englewood Clifts, NJ.
    • Hildebrand, J. H.; Prousnitz, J. M.; Scott, R. L. Regular and Related Solutions; Van Nostrand-Reinhold; Princeton, 1970. Hildebrand, J. H.; Scott, R. L. Regular Solutions; Prentice-Hall: Englewood Clifts, NJ., 1962. The solvent CED is the solvent heat of vaporization minus RT divided by the molar volume. For water the value in pressure units is 22,000 atm!
    • (1962) Regular Solutions
    • Hildebrand, J.H.1    Scott, R.L.2
  • 37
    • 0642385685 scopus 로고
    • Rideout, D.; Breslow, R. J. Am. Chem. Soc. 1980, 102, 5613. Grieco, P. A.; Garner, P.; He, Z. Tetrahedron Lett. 1983, 24, 1897. Breslow, R. Acc. Chem. Res. 1991, 24, 159. Blokzijl, W.; Engberts, J. B. F. N. J. Am. Chem. Soc.1992, 114, 5440. Breslow, R.; Zhu, Z. J. Am. Chem. Soc. 1995, 117, 9923. For references to negative activation volumes in Diels-Alder reactions see: LeNoble, W. J. Chem. Rev. 1989, 89, 549.
    • (1980) J. Am. Chem. Soc. , vol.102 , pp. 5613
    • Rideout, D.1    Breslow, R.2
  • 38
    • 0000619653 scopus 로고
    • Rideout, D.; Breslow, R. J. Am. Chem. Soc. 1980, 102, 5613. Grieco, P. A.; Garner, P.; He, Z. Tetrahedron Lett. 1983, 24, 1897. Breslow, R. Acc. Chem. Res. 1991, 24, 159. Blokzijl, W.; Engberts, J. B. F. N. J. Am. Chem. Soc.1992, 114, 5440. Breslow, R.; Zhu, Z. J. Am. Chem. Soc. 1995, 117, 9923. For references to negative activation volumes in Diels-Alder reactions see: LeNoble, W. J. Chem. Rev. 1989, 89, 549.
    • (1983) Tetrahedron Lett. , vol.24 , pp. 1897
    • Grieco, P.A.1    Garner, P.2    He, Z.3
  • 39
    • 0001069588 scopus 로고
    • Rideout, D.; Breslow, R. J. Am. Chem. Soc. 1980, 102, 5613. Grieco, P. A.; Garner, P.; He, Z. Tetrahedron Lett. 1983, 24, 1897. Breslow, R. Acc. Chem. Res. 1991, 24, 159. Blokzijl, W.; Engberts, J. B. F. N. J. Am. Chem. Soc.1992, 114, 5440. Breslow, R.; Zhu, Z. J. Am. Chem. Soc. 1995, 117, 9923. For references to negative activation volumes in Diels-Alder reactions see: LeNoble, W. J. Chem. Rev. 1989, 89, 549.
    • (1991) Acc. Chem. Res. , vol.24 , pp. 159
    • Breslow, R.1
  • 40
    • 0000888091 scopus 로고
    • Rideout, D.; Breslow, R. J. Am. Chem. Soc. 1980, 102, 5613. Grieco, P. A.; Garner, P.; He, Z. Tetrahedron Lett. 1983, 24, 1897. Breslow, R. Acc. Chem. Res. 1991, 24, 159. Blokzijl, W.; Engberts, J. B. F. N. J. Am. Chem. Soc.1992, 114, 5440. Breslow, R.; Zhu, Z. J. Am. Chem. Soc. 1995, 117, 9923. For references to negative activation volumes in Diels-Alder reactions see: LeNoble, W. J. Chem. Rev. 1989, 89, 549.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 5440
    • Blokzijl, W.1    Engberts, J.B.F.N.2
  • 41
    • 0000586983 scopus 로고
    • Rideout, D.; Breslow, R. J. Am. Chem. Soc. 1980, 102, 5613. Grieco, P. A.; Garner, P.; He, Z. Tetrahedron Lett. 1983, 24, 1897. Breslow, R. Acc. Chem. Res. 1991, 24, 159. Blokzijl, W.; Engberts, J. B. F. N. J. Am. Chem. Soc.1992, 114, 5440. Breslow, R.; Zhu, Z. J. Am. Chem. Soc. 1995, 117, 9923. For references to negative activation volumes in Diels-Alder reactions see: LeNoble, W. J. Chem. Rev. 1989, 89, 549.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 9923
    • Breslow, R.1    Zhu, Z.2
  • 42
    • 33845184910 scopus 로고
    • Rideout, D.; Breslow, R. J. Am. Chem. Soc. 1980, 102, 5613. Grieco, P. A.; Garner, P.; He, Z. Tetrahedron Lett. 1983, 24, 1897. Breslow, R. Acc. Chem. Res. 1991, 24, 159. Blokzijl, W.; Engberts, J. B. F. N. J. Am. Chem. Soc.1992, 114, 5440. Breslow, R.; Zhu, Z. J. Am. Chem. Soc. 1995, 117, 9923. For references to negative activation volumes in Diels-Alder reactions see: LeNoble, W. J. Chem. Rev. 1989, 89, 549.
    • (1989) Chem. Rev. , vol.89 , pp. 549
    • LeNoble, W.J.1
  • 45
    • 0000884859 scopus 로고
    • and references therein
    • Mills, S. G.; Beak, P. J. Org. Chem. 1985, 50, 1216 and references therein.
    • (1985) J. Org. Chem. , vol.50 , pp. 1216
    • Mills, S.G.1    Beak, P.2
  • 52
    • 0000703656 scopus 로고
    • Gao, J. J. Am. Chem. Soc. 1994, 116, 1563. See also: Gao, J. Acc. Chem. Res. 1996, 29, 298.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 1563
    • Gao, J.1
  • 53
    • 0001491955 scopus 로고    scopus 로고
    • Gao, J. J. Am. Chem. Soc. 1994, 116, 1563. See also: Gao, J. Acc. Chem. Res. 1996, 29, 298.
    • (1996) Acc. Chem. Res. , vol.29 , pp. 298
    • Gao, J.1
  • 61
    • 33847799798 scopus 로고
    • Ireland, R. E.; Mueller, R. H.; Willard, A. K. J. Am. Chem. Soc. 1976, 98, 2868. Denmark, S. E.; Harmata, M. A. J. Am. Chem. Soc. 1982, 104, 4972. Wick, A. E.; Felix, D.; Steen, K.; Eschenmoser, A. Helv. Chim. Acta. 1964, 47, 2425. Faulkner, D. J.; Petersen, M. R. J. Am. Chem. Soc. 1973, 95, 553. Normant, J. F.; Reboul, O.; Sauvetre, R.; Deshayes, H.; Masure, D.; Villieras, J. Bull. Soc. Chim. Fr. 1974, 2072.
    • (1976) J. Am. Chem. Soc. , vol.98 , pp. 2868
    • Ireland, R.E.1    Mueller, R.H.2    Willard, A.K.3
  • 62
    • 33845552784 scopus 로고
    • Ireland, R. E.; Mueller, R. H.; Willard, A. K. J. Am. Chem. Soc. 1976, 98, 2868. Denmark, S. E.; Harmata, M. A. J. Am. Chem. Soc. 1982, 104, 4972. Wick, A. E.; Felix, D.; Steen, K.; Eschenmoser, A. Helv. Chim. Acta. 1964, 47, 2425. Faulkner, D. J.; Petersen, M. R. J. Am. Chem. Soc. 1973, 95, 553. Normant, J. F.; Reboul, O.; Sauvetre, R.; Deshayes, H.; Masure, D.; Villieras, J. Bull. Soc. Chim. Fr. 1974, 2072.
    • (1982) J. Am. Chem. Soc. , vol.104 , pp. 4972
    • Denmark, S.E.1    Harmata, M.A.2
  • 63
    • 84984088671 scopus 로고
    • Ireland, R. E.; Mueller, R. H.; Willard, A. K. J. Am. Chem. Soc. 1976, 98, 2868. Denmark, S. E.; Harmata, M. A. J. Am. Chem. Soc. 1982, 104, 4972. Wick, A. E.; Felix, D.; Steen, K.; Eschenmoser, A. Helv. Chim. Acta. 1964, 47, 2425. Faulkner, D. J.; Petersen, M. R. J. Am. Chem. Soc. 1973, 95, 553. Normant, J. F.; Reboul, O.; Sauvetre, R.; Deshayes, H.; Masure, D.; Villieras, J. Bull. Soc. Chim. Fr. 1974, 2072.
    • (1964) Helv. Chim. Acta , vol.47 , pp. 2425
    • Wick, A.E.1    Felix, D.2    Steen, K.3    Eschenmoser, A.4
  • 64
    • 0015934140 scopus 로고
    • Ireland, R. E.; Mueller, R. H.; Willard, A. K. J. Am. Chem. Soc. 1976, 98, 2868. Denmark, S. E.; Harmata, M. A. J. Am. Chem. Soc. 1982, 104, 4972. Wick, A. E.; Felix, D.; Steen, K.; Eschenmoser, A. Helv. Chim. Acta. 1964, 47, 2425. Faulkner, D. J.; Petersen, M. R. J. Am. Chem. Soc. 1973, 95, 553. Normant, J. F.; Reboul, O.; Sauvetre, R.; Deshayes, H.; Masure, D.; Villieras, J. Bull. Soc. Chim. Fr. 1974, 2072.
    • (1973) J. Am. Chem. Soc. , vol.95 , pp. 553
    • Faulkner, D.J.1    Petersen, M.R.2
  • 65
    • 0001874594 scopus 로고
    • Ireland, R. E.; Mueller, R. H.; Willard, A. K. J. Am. Chem. Soc. 1976, 98, 2868. Denmark, S. E.; Harmata, M. A. J. Am. Chem. Soc. 1982, 104, 4972. Wick, A. E.; Felix, D.; Steen, K.; Eschenmoser, A. Helv. Chim. Acta. 1964, 47, 2425. Faulkner, D. J.; Petersen, M. R. J. Am. Chem. Soc. 1973, 95, 553. Normant, J. F.; Reboul, O.; Sauvetre, R.; Deshayes, H.; Masure, D.; Villieras, J. Bull. Soc. Chim. Fr. 1974, 2072.
    • (1974) Bull. Soc. Chim. Fr. , pp. 2072
    • Normant, J.F.1    Reboul, O.2    Sauvetre, R.3    Deshayes, H.4    Masure, D.5    Villieras, J.6
  • 70
    • 0008180513 scopus 로고
    • Gajewski, J. J.; Emrani, J. J. Am. Chem. Soc. 1984, 106, 5733. Kupczyk-Subotkowska, L.; Saunders, W. H., Jr.; Shine, H. J.; Subotkowski, W. J. Am. Chem. Soc. 1994, 116, 7088. The results of these two studies on 2-(trimethylsilyl)oxy]allyl vinyl ether using deuterium and heavy atom isotope effects, respectively, are in near-quantitative agreement without the corrections suggested by us in ref 8.
    • (1984) J. Am. Chem. Soc. , vol.106 , pp. 5733
    • Gajewski, J.J.1    Emrani, J.2
  • 71
    • 0344994432 scopus 로고
    • Gajewski, J. J.; Emrani, J. J. Am. Chem. Soc. 1984, 106, 5733. Kupczyk-Subotkowska, L.; Saunders, W. H., Jr.; Shine, H. J.; Subotkowski, W. J. Am. Chem. Soc. 1994, 116, 7088. The results of these two studies on 2-(trimethylsilyl)oxy]allyl vinyl ether using deuterium and heavy atom isotope effects, respectively, are in near-quantitative agreement without the corrections suggested by us in ref 8.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 7088
    • Kupczyk-Subotkowska, L.1    Saunders Jr., W.H.2    Shine, H.J.3    Subotkowski, W.4


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